HCID 56620044, compound → HCID 56637805, compound

HRID 1974635Notes

Reaction equation

HRID 1974635 reaction equation
C([O:8][N:9]1[C:46](=[O:47])[CH:45]=[C:12]2[N:13]([CH:42]3[CH2:44][CH2:43]3)[C:14]3[CH:19]=[C:18]([N:20]4[CH2:25][CH2:24][N:23]([C:26]([C@@H:28]([NH:30]C(=O)OCC5C=CC=CC=5)[CH3:29])=[O:27])[CH2:22][CH2:21]4)[C:17]([F:41])=[CH:16][C:15]=3[N:11]2[C:10]1=[O:48])C1C=CC=CC=1>CN(C=O)C.[Pd]>[NH2:30][C@H:28]([C:26]([N:23]1[CH2:22][CH2:21][N:20]([C:18]2[C:17]([F:41])=[CH:16][C:15]3[N:11]4[C:10](=[O:48])[N:9]([OH:8])[C:46](=[O:47])[CH:45]=[C:12]4[N:13]([CH:42]4[CH2:44][CH2:43]4)[C:14]=3[CH:19]=2)[CH2:25][CH2:24]1)=[O:27])[CH3:29]

Participants

4

Reactant 1

HCID 56620044HCID 56620044, compound

Product 1

HCID 56637805HCID 56637805, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 23938PalladiumSolvent

Procedure

Benzyl [(S)-1-[[4-[2-(benzyloxy)-5-cyclopropyl-8-fluoro-1,2,3,5-tetrahydro-1,3-dioxopyrimido[1,6-a]benzimidazol-7-yl]-1-piperazinyl]carbonyl]ethyl]carbamate (127 mg, 0.194 mmol) is dissolved in DMF (15 ml) and hydrogenated over 5 percent Pd/C. After completion of the reduction the catalyst is filtered off and the filtrate is evaporated. The residue is taken up in methanol (50 ml) and treated with active charcoal. After filtering off the charcoal the filtrate is concentrated to a volume of 25 ml. The separated crystals are filtered off. There are obtained 62 mg (84%) of 7-(4-L-alanyl-1-piperazinyl)-5-cyclopropyl-8-fluoro-2-hydroxypyrimido[1,6-a]benzimidazole-1,3(2H,5H)-dione.

Workup

  1. filtrationAfter completion of the reduction the catalyst is filtered off
  2. customthe filtrate is evaporated
  3. additiontreated with active charcoal
  4. filtrationAfter filtering off the charcoal the filtrate
  5. concentrationis concentrated to a volume of 25 ml
  6. filtrationThe separated crystals are filtered off

Sources & evidence

ORD record
ord-b700337c10794be98e3f0b8b60429868
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

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